This qualitative case study has dealt with three open concepts of urban slum dwellers, information and communication technologies, ICT, and occupation to understand their relation in the context of Chennai, India inner city slum area. Through interviews with 22 dwellers and 4 local professionals, the study finds that the already unequal structures rooted in the hierarchical Indian caste system causes inequity in outcome of education and access to occupation, which the introduction of ICT into almost all arenas of social life is expected to overcome. Due to ICT’s role as a facilitator, not an end in itself and the ‘glass walls and ceilings’ blocking access to the private sector industry that locate the aspired-for IT jobs, ICT is argued to not wash out inequality between the social groups. The policy and urban governance is found to have an ambivalent role in their aid of the underprivileged, as low caste stigma has been institutionalised and thus become both a social and political reality. With the theoretical concepts of Pierre Bourdieu and Manuel Castells, the slum as a place is argued to be an expression of symbolic violence, and the Network Society notion functions as an understanding of the urban transformations in occupation, education advances and social life ICT has brought about.